#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2013071.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2013071
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o730
_journal_page_last  o732
_publ_section_title
;
2,4-Diamino-5-(1-naphthyl)-3,5-diaza-1-azoniaspiro[5.5]undeca-1,3-diene
chloride
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_[local]_cod_cif_authors_sg_H-M  'I 2/a'
loop_
_publ_author_name
  'Papandreou, Nikolaos C.'
  'Makedonopoulou, Stella'
  'Antoniadou-Vyza, Ekaterini A.'
  'Mavridis, Irene M.'
  'Hamodrakas, Stavros J.'
_chemical_name_common
 '2,4-diamino-5-naphthalen-1-yl-3,5-diaza-1-azoniaspiro[5.5]undeca-1,3-diene Cl'
_chemical_formula_moiety  'C18 H22 N5 + , Cl -'
_chemical_formula_sum  'C18 H22 Cl N5'
_chemical_formula_weight  343.86
_chemical_melting_point  402
_symmetry_cell_setting  Monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x+1/2, -y, z'
  'x+1/2, y+1/2, z+1/2'
  'x+1, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x-1/2, y, -z'
  '-x+1/2, -y+1/2, -z+1/2'
  '-x, y+1/2, -z+1/2'
_cell_length_a  24.862(4)
_cell_length_b  7.3778(14)
_cell_length_c  19.633(4)
_cell_angle_alpha  90
_cell_angle_beta  101.823(6)
_cell_angle_gamma  90
_cell_volume  3524.8(11)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.296
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  C1 0.56136(10) 0.2232(4) 0.00190(12) 0.0355(6) Uani d . 1 . . C
  N1 0.55678(10) 0.1314(3) 0.05788(11) 0.0447(6) Uani d . 1 . . N
  H1A 0.5771 0.1588 0.0975 0.068(11) Uiso calc R 1 . . H
  H1B 0.5335 0.0441 0.0548 0.044(8) Uiso calc R 1 . . H
  N2 0.52821(9) 0.1751(3) -0.05896(10) 0.0360(5) Uani d . 1 . . N
  C3 0.54354(10) 0.2333(3) -0.11681(13) 0.0343(5) Uani d . 1 . . C
  N3 0.51588(10) 0.1807(3) -0.17842(11) 0.0462(6) Uani d . 1 . . N
  H3A 0.4881 0.1094 -0.1813 0.056(10) Uiso calc R 1 . . H
  H3B 0.5256 0.2178 -0.2156 0.053(9) Uiso calc R 1 . . H
  N4 0.58752(9) 0.3416(3) -0.11374(10) 0.0369(5) Uani d . 1 . . N
  H4 0.6074 0.3359 -0.1447 0.15(2) Uiso calc R 1 . . H
  C5 0.60021(10) 0.4690(4) -0.05602(12) 0.0362(6) Uani d . 1 . . C
  N6 0.59798(9) 0.3601(3) 0.00714(10) 0.0392(5) Uani d . 1 . . N
  C7 0.62873(11) 0.4215(4) 0.07370(14) 0.0436(6) Uani d DU 1 . . C
  C8 0.60993(14) 0.5612(4) 0.10914(15) 0.0529(7) Uani d DU 1 . . C
  H8 0.5750 0.6079 0.0920 0.063(10) Uiso calc R 1 . . H
  C9 0.64139(15) 0.6354(5) 0.17002(17) 0.0673(9) Uani d DU 1 . . C
  H9 0.6280 0.7304 0.1929 0.090(14) Uiso calc R 1 . . H
  C10 0.69313(16) 0.5629(5) 0.19520(18) 0.0722(10) Uani d DU 1 . . C
  H10 0.7147 0.6111 0.2355 0.065(10) Uiso calc R 1 . . H
  C11 0.71399(11) 0.4176(4) 0.16133(14) 0.0510(7) Uani d DU 1 . . C
  C12 0.68026(12) 0.3433(4) 0.10014(14) 0.0505(7) Uani d DU 1 . . C
  C13 0.70035(13) 0.1917(4) 0.06703(16) 0.0550(8) Uani d DU 1 . . C
  H13 0.6795 0.1390 0.0272 0.057(10) Uiso calc R 1 . . H
  C14 0.75161(14) 0.1279(6) 0.0966(2) 0.0736(10) Uani d DU 1 . . C
  H14 0.7651 0.0288 0.0761 0.104(17) Uiso calc R 1 . . H
  C15 0.78433(16) 0.2021(7) 0.1551(2) 0.0875(13) Uani d DU 1 . . C
  H15 0.8190 0.1546 0.1728 0.14(2) Uiso calc R 1 . . H
  C16 0.76559(14) 0.3438(6) 0.1865(2) 0.0767(11) Uani d DU 1 . . C
  H16 0.7877 0.3936 0.2260 0.23(4) Uiso calc R 1 . . H
  C17 0.65773(11) 0.5475(4) -0.05267(14) 0.0424(6) Uani d . 1 . . C
  H17A 0.6685 0.6176 -0.0103 0.059(10) Uiso calc R 1 . . H
  H17B 0.6838 0.4491 -0.0512 0.041(8) Uiso calc R 1 . . H
  C18 0.65981(12) 0.6686(4) -0.11528(16) 0.0500(7) Uani d . 1 . . C
  H18A 0.6959 0.7238 -0.1092 0.051(8) Uiso calc R 1 . . H
  H18B 0.6542 0.5949 -0.1571 0.065(10) Uiso calc R 1 . . H
  C19 0.61629(15) 0.8168(4) -0.12421(19) 0.0599(8) Uani d . 1 . . C
  H19A 0.6169 0.8847 -0.1663 0.073(11) Uiso calc R 1 . . H
  H19B 0.6245 0.8998 -0.0852 0.065(11) Uiso calc R 1 . . H
  C20 0.55942(13) 0.7361(4) -0.12847(17) 0.0533(7) Uani d . 1 . . C
  H20A 0.5326 0.8330 -0.1321 0.065(10) Uiso calc R 1 . . H
  H20B 0.5499 0.6618 -0.1700 0.059(10) Uiso calc R 1 . . H
  C21 0.55736(12) 0.6215(4) -0.06496(15) 0.0439(6) Uani d . 1 . . C
  H21A 0.5210 0.5693 -0.0696 0.055(9) Uiso calc R 1 . . H
  H21B 0.5642 0.6978 -0.0238 0.058(9) Uiso calc R 1 . . H
  Cl1 0.58605(3) 0.39422(11) -0.27703(3) 0.0488(2) Uani d . 1 . . Cl
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  C1 0.0384(13) 0.0408(14) 0.0286(12) -0.0008(11) 0.0094(10) -0.0001(10)
  N1 0.0499(13) 0.0569(14) 0.0269(11) -0.0140(11) 0.0073(9) 0.0037(10)
  N2 0.0401(11) 0.0399(12) 0.0275(10) -0.0054(9) 0.0061(8) -0.0001(9)
  C3 0.0399(13) 0.0327(12) 0.0295(12) -0.0007(10) 0.0053(10) 0.0005(10)
  N3 0.0583(14) 0.0513(14) 0.0274(11) -0.0160(12) 0.0053(10) 0.0021(10)
  N4 0.0433(12) 0.0407(12) 0.0281(10) -0.0059(10) 0.0107(9) -0.0025(9)
  C5 0.0412(13) 0.0400(14) 0.0275(12) -0.0070(11) 0.0069(10) -0.0014(10)
  N6 0.0433(12) 0.0471(13) 0.0263(10) -0.0109(10) 0.0054(9) 0.0002(9)
  C7 0.0449(14) 0.0502(16) 0.0350(13) -0.0029(12) 0.0063(11) -0.0005(12)
  C8 0.0652(19) 0.0539(17) 0.0418(15) 0.0043(15) 0.0161(13) -0.0074(13)
  C9 0.084(2) 0.070(2) 0.0453(17) -0.0040(19) 0.0093(16) -0.0110(16)
  C10 0.084(2) 0.082(2) 0.0457(18) -0.020(2) 0.0011(17) -0.0031(17)
  C11 0.0443(15) 0.069(2) 0.0369(14) -0.0139(14) 0.0016(12) 0.0106(13)
  C12 0.0445(15) 0.0653(19) 0.0421(15) -0.0043(14) 0.0093(12) 0.0155(14)
  C13 0.0553(17) 0.0624(19) 0.0508(17) 0.0167(15) 0.0188(14) 0.0122(15)
  C14 0.062(2) 0.093(3) 0.070(2) 0.0258(19) 0.0233(17) 0.031(2)
  C15 0.054(2) 0.129(4) 0.080(3) 0.011(2) 0.0142(18) 0.050(3)
  C16 0.0477(18) 0.113(3) 0.068(2) -0.0075(19) 0.0080(16) 0.035(2)
  C17 0.0403(14) 0.0472(15) 0.0400(14) -0.0092(12) 0.0090(11) -0.0006(12)
  C18 0.0523(17) 0.0504(17) 0.0510(17) -0.0133(13) 0.0188(13) 0.0006(14)
  C19 0.076(2) 0.0434(17) 0.066(2) -0.0032(16) 0.0273(17) 0.0081(16)
  C20 0.0618(18) 0.0460(16) 0.0539(17) 0.0094(15) 0.0159(14) 0.0071(14)
  C21 0.0482(16) 0.0424(15) 0.0435(15) -0.0009(12) 0.0153(12) -0.0036(12)
  Cl1 0.0519(4) 0.0653(5) 0.0288(3) 0.0050(3) 0.0072(3) 0.0036(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C1 N1 . 1.316(3) yes
  C1 N2 . 1.352(3) yes
  C1 N6 . 1.350(3) yes
  N2 C3 . 1.340(3) yes
  N3 C3 . 1.321(3) yes
  N4 C3 . 1.346(3) yes
  N4 C5 . 1.456(3) yes
  N6 C5 . 1.488(3) yes
  N6 C7 . 1.445(3) yes
  C5 C17 . 1.532(4) yes
  C5 C21 . 1.535(4) yes
  C7 C8 . 1.378(4) no
  C7 C12 . 1.404(4) no
  C8 C9 . 1.399(4) no
  C9 C10 . 1.387(4) no
  C10 C11 . 1.414(4) no
  N1 H1A . 0.8600 no
  N1 H1B . 0.8600 no
  N3 H3A . 0.8600 no
  N3 H3B . 0.8600 no
  N4 H4 . 0.8600 no
  C8 H8 . 0.9300 no
  C9 H9 . 0.9300 no
  C10 H10 . 0.9300 no
  C11 C16 . 1.388(4) no
  C11 C12 . 1.427(4) no
  C12 C13 . 1.434(4) no
  C13 C14 . 1.371(4) no
  C13 H13 . 0.9300 no
  C14 C15 . 1.378(5) no
  C14 H14 . 0.9300 no
  C15 C16 . 1.344(5) no
  C15 H15 . 0.9300 no
  C16 H16 . 0.9300 no
  C17 C18 . 1.529(4) no
  C17 H17A . 0.9700 no
  C17 H17B . 0.9700 no
  C18 C19 . 1.523(5) no
  C18 H18A . 0.9700 no
  C18 H18B . 0.9700 no
  C19 C20 . 1.521(5) no
  C19 H19A . 0.9700 no
  C19 H19B . 0.9700 no
  C20 C21 . 1.516(4) no
  C20 H20A . 0.9700 no
  C20 H20B . 0.9700 no
  C21 H21A . 0.9700 no
  C21 H21B . 0.9700 no